Cooperative Noncovalent Interactions Lead to a Highly Diastereoselective Sulfonyl-Directed Fluorination of Steroidal α,β-Unsaturated Hydrazones

被引：6

作者：

Capilato, Joseph N. ^{[1
]}

Siegler, Maxime A. ^{[1
]}

Rowshanpour, Rozhin ^{[2
]}

Dudding, Travis ^{[2
]}

Lectka, Thomas ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Charles & 34Th St, Baltimore, MD 21218 USA

[2] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

基金：

加拿大自然科学与工程研究理事会; 美国国家科学基金会;

关键词：

SITE; KETONES; PATH;

D O I：

10.1021/acs.joc.0c02716

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of steroidal alpha,beta-unsaturated hydrazones is presented whose behavior and reactivity are governed by various types of weak C-H hydrogen bonds. Several interesting features in a representative X-ray crystal structure and H-1 NMR spectrum are examined that provide evidence for a unique bifurcated intramolecular C-H interaction. Moreover, these steroid derivatives undergo functionalization in the form of a highly regio- and stereoselective fluorination; the sulfonyl oxygen atoms are proposed to direct the fluorinating reagent through C-H hydrogen bonds.

引用

页码：1300 / 1307

页数：8